Ethyl 3-ethoxycrotonate

Base Information

• Chemical Name: Ethyl 3-ethoxycrotonate
• CAS No.: 998-91-4
• Molecular Formula: C8H14 O3
• Molecular Weight: 158.197
• Hs Code.: 2918990090
• European Community (EC) Number: 213-652-8
• DSSTox Substance ID: DTXSID101304535
• Nikkaji Number: J133.518I,J552.754F
• Mol file: 998-91-4.mol

Synonyms:Ethyl 3-ethoxycrotonate;998-91-4;3-Ethoxy-2-butenoic acid ethyl ester;Ethyl 3-ethoxybut-2-enoate;Crotonic acid, 3-ethoxy-, ethyl ester;ethyl beta-ethoxycrotonate;(Z)-Ethyl 3-ethoxybut-2-enoate;3-Ethoxycrotonic acid ethyl ester;ethyl (2Z)-3-ethoxy-2-butenoate;2-Butenoic acid, 3-ethoxy-, ethyl ester;SCHEMBL221523;ZOCYCSPSSNMXBU-SREVYHEPSA-N;DTXSID101304535;(Z)-3-ethoxy-but-2-enoic acid ethyl ester

Chemical Property of Ethyl 3-ethoxycrotonate

Chemical Property:

• Vapor Pressure: 0.203mmHg at 25°C
• Melting Point: 30-32 °C(lit.)
• Refractive Index: 1.4535
• Boiling Point: 195-200 °C(lit.)
• Flash Point: 58.3°C
• PSA: 35.53000
• Density: 0.965g/cm³
• LogP: 1.48980
• Water Solubility.: Insoluble in water.
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 158.094294304
• Heavy Atom Count: 11
• Complexity: 149

Purity/Quality:

98%min ^*data from raw suppliers

Ethyl 3-ethoxycrotonate ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-27-36/37/39-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=CC(=O)OCC)C
• Isomeric SMILES: CCO/C(=C\C(=O)OCC)/C
• Uses: Ethyl 3-ethoxy-2-butenoate is used as pharmaceutical intermediate.

Technology Process of Ethyl 3-ethoxycrotonate

There total 38 articles about Ethyl 3-ethoxycrotonate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 85.0%

ethyl acetoacetate (141-97-9) + orthoformic acid triethyl ester (122-51-0) → ethyl 3-ethoxy-2-butenoate (998-91-4)

Guidance literature:

ethyl acetoacetate; With sulfuric acid; In ethanol; at 50 ℃; Inert atmosphere;

orthoformic acid triethyl ester; at 50 ℃; for 16h;

Reference yield: 53.0%

ethyl bromide (74-96-4) + ethyl acetoacetate (141-97-9) → ethyl 3-ethoxy-2-butenoate (998-91-4) + ethyl 2,2-diethyl-3-oxobutanoate (1619-57-4) + ethyl 2-ethyl-3-oxobutanoate (607-97-6)

Guidance literature:

With aluminum oxide; sodium ethanolate; Yields of byproduct given. Title compound not separated from byproducts; 2.) room temperature, 5 d;

Reference yield: 50.0%

ethyl acetoacetate (141-97-9) + orthoformic acid triethyl ester (122-51-0) → ethyl 3-ethoxy-2-butenoate (998-91-4) + formic acid ethyl ester (109-94-4)

Guidance literature:

With toluene-4-sulfonic acid; In ethanol; at 65 ℃;

DOI:10.1016/S0008-6215(99)00118-4

upstream raw materials:

3,3-diethoxybutyric acid ethyl ester

ethyl acetoacetate

acetyl chloride

orthoformic acid triethyl ester

Downstream raw materials:

5-methyl-4-hepten-3-one

2,6-dihydroxy-3-cyano-4-methylpyrimidine

Δ²-3-ethoxybutenoic acid

ethyl 2-hydroxyimino-3-oxobutanoate

Refernces

• 1、 Ndong, Ella,Judicael, Guy,Parrain, Jean Luc,Abarbri, Mohamed. "Regioselective Synthesis of α-Perfluoroalkylated Ketals via Double Michael Addition of Alcohols to Activated Alkynes". . p. 2635 - 2640. Retrieved 2015.
• 2、 -. "INHIBITORS OF HIV REPLICATION". Page/Page column 23. . Retrieved 2012/06/01.